Quitting Big Law for a Startup: Family Dinner with Payton McCoy

When Payton McCoy’s Big Law supervisor saw the product McCoy built, he advised him to quit his job to pursue it.

McCoy, who spoke to Residents at The Garage on Tuesday, co-founded an artificial intelligence platform called Greenshoe designed to streamline company disclosures to the Securities and Exchange Commission. After attending Columbia Law School and working at two of the top law firms in the United States, McCoy decided to pivot his career from advising other companies to building his own.

“I have a really interesting founder story. I don't think a lot of people go through law school and then decide, ‘okay, I'm going to quit all of that and just start a risky company,’” McCoy said.

Public companies  are obligated to regularly disclose information about their finances and operations, but McCoy said those disclosures are difficult to put together and inefficient to send out quarterly and annually. Instead, Greenshoe is building infrastructure that will eventually enable real-time disclosure in line with changing SEC guidelines. 

As a former attorney, McCoy said his legal background makes him approach starting a business from a unique perspective — given the detail-oriented nature of law, McCoy said he has learned to perfect even the smallest emails. This can prove both useful and limiting in the world of entrepreneurship.

“There are so many things from law school and also practicing that make me a better founder,” McCoy said. “There's also a lot of things I feel like I've had to unlearn. There is a culture at startups, especially software, where you need to ship things super fast, and you actually don't want to spend so much time perfecting things.”

McCoy said he always had a passion for entrepreneurship and wanted to take advantage of the rise of AI. He equated AI with the dot-com boom of the late 1990s, advising founders that now is a good time to build. McCoy also acknowledged the risks of AI hallucination, especially in court cases. Greenshoe requires a human in the loop to ensure accuracy.

“When our AI system recommends an output or when it completes a document, it has to be grounded in something,” McCoy said. “Every time something happens, a person has to sign off on it.”

As AI rapidly improves its capabilities, McCoy said he feels pressure to advance Greenshoe as soon as possible to match the industry’s developments.

“I think about speed and time,” McCoy said. “We need to build faster. We need to go faster. We need to ship faster. I want to get the product out so we can iterate.”

McCoy advised founders to take advantage of AI, sharing that AI tools enabled him to keep his startup lean. He also suggested they tailor their hiring practices by creating a mock assignment to understand how applicants think in order to build a team with both technical knowledge and emotional intelligence.

McCoy said that one of the greatest lessons he learned was to remain open-minded to nontraditional routes.

“There are a lot of different ways to start a company. I think when you're starting one, you often map yourself onto one particular way,” McCoy said. “I want people to know that there are lots of different paths to success.”